Water → 6-bromo-3,4-dihydro-1H-2lambda6,1-benzothiazine-2,2-dione

HRID 58861노트

반응식

HRID 58861 반응식
C1C(=O)N([Br:8])C(=O)C1.[NH:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][S:10]1(=[O:20])=[O:19].O.CCOC(C)=O>CN(C=O)C>[Br:8][C:17]1[CH:16]=[CH:15][C:14]2[NH:9][S:10](=[O:19])(=[O:20])[CH2:11][CH2:12][C:13]=2[CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 122033353192-06-1

생성물 1

HCID 691080756-bromo-3,4-dihydro-1H-2lambda6,1-benzothiazine-2,2-dione수율 79.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

NBS (1.5 g, 8.2 mmol) was added to a solution of 3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide (1.5 g, 8.2 mmol) in DMF (15 mL). The reaction mixture was stirred overnight at ambient temperature followed by addition of water (200 mL) and EtOAc (100 mL). The two layers were separated and the aqueous phase was extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (200 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3) to afford 6-bromo-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide (1.7 g, 79% yield).

후처리

  1. customThe two layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (100 mL×3)
  3. washThe combined organic phases were washed with brine (200 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3)

출처 및 근거

ORD 기록
ord-c88953e3d60947be945fb965a6c5a488
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434761B2

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